Phthalimide → 2-(3-(3-(Biphenyl-3-ylethynyl)phenyl)propyl)isoindoline-1,3-dione

HRID 2098488Notes

Reaction equation

HRID 2098488 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17]O)[CH:12]=[CH:13][CH:14]=2)[CH:2]=1.[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12>>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][N:29]3[C:25](=[O:35])[C:26]4[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:28]3=[O:30])[CH:12]=[CH:13][CH:14]=2)[CH:2]=1

Participants

3

Reactant 2

HCID 6809PhthalimideHCID 576085113-(3-(Biphenyl-3-ylethynyl)phenyl)propan-1-ol

Product 1

HCID 576085282-(3-(3-(Biphenyl-3-ylethynyl)phenyl)propyl)isoindoline-1,3-dione

Procedure

Coupling of 3-(3-(biphenyl-3-ylethynyl)phenyl)propan-1-ol with phthalimide was conducted following the method described in Example 21. Purification by flash chromatography (6% EtOAc-hexanes) gave 2-(3-(3-(biphenyl-3-ylethynyl)phenyl)propyl)isoindoline-1,3-dione. Yield (0.320 g, 42%): 1H NMR (400 MHz, CDCl3) δ 7.84 (dd, J=5.6, 3.2 Hz, 2H), 7.77 (m, 1H), 7.71 (dd, J=5.6, 3.2 Hz, 2H), 7.61-7.63 (m, 2H), 7.32-7.57 (m, 8H), 7.18-7.25 (m, 2H), 3.77 (t, J=7.2 Hz, 2H), 2.70 (t, J=7.2 Hz, 2H), 2.02-2.09 (m, 2H).

Workup

  1. customPurification by flash chromatography (6% EtOAc-hexanes)

Sources & evidence

ORD record
ord-d4613b521aa5401ea78385edf20f47bf
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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